Thank you all for your well thought out answers. I feel much more equipped to speak with him again.

I've recently given in to the idea of universal healthcare even though I don't I necessarily agree with it. I believe it's the only way to cover everyone but also know it's going to to just create a higher tax bill and be administered by idiots. Look at the VA. My point of view is from someone who has paid for private insurance his entire life and never received a government benefit of any kind. After 25 years of paying for my own insurance AND paying a ton of taxes that go towards keeping everybody healthy that doesn't have insurance, I'm ready for somthing free.

As far as education, no I don't believe it should be free. With heathcare the money spent is a need, education is optional. Everybody needs healthcare, not every body needs a college degree. What reading I've done indicates that a high percentage of students that start college either never finish or do not take jobs in the field they studied for. There's a lot of tax dollars wasted there already. I believe every student should be responsible for the debt their education created and the job that education provided should repay that debt. If the student isn't held responsible for the debt they don't have to use the education they received. If they don't use it why give it to them. The biggest pro for free education is that everybody can go to college but that is also the biggest con. If everybody gets a degree

Whew! I'm staying out of this..lol.

Two facts:

1. the USA is the only industrialized nation in the entire world that does not show enough concern for the well-being of its people to provide universal healthcare. All the resty do it. We can and should, as well.

2. Research shows that investment in the GI Bill at the end of World War II resulted in at least a 40.0 percent growth in our nation's productivity. Full investment in the education of ALL people who want more knowledge and skills WILL inevitably result in higher prosperity and economic growth. And one who says otherwise is either lying or ignorant.

Argument strategy often depends on the actual underlying values of the person(s) you are trying to persuade. Are they coming from an attitude of "everyone for him/herself?" Are they moralists who fret over "undeserving" people possibly receiving services they haven't "earned?" Do they see the economic world as a zero-sum paradigm in which one person's benefit automatically equals another's loss?
It's hard for me to wrap my head around any of those viewpoints, because to me universal healthcare and quality public education are hallmarks of a civil society. If your target audience is fixated on the idea of "fairness" and claims people have to "earn" these services, you might point out that the whole value concept of fairness is subjective and ever-shifting. Humans are quick to believe we "deserve" the good things that come our way, but that the difficult things aren't "fair." For moralizers, that dynamic oddly changes when their focus shifts to other people. Suddenly they are worried about those others receiving "unfair" advantages.
If your target audience is Christian, you might point out just how socialistic their guru Jesus was. They won't like that cognitive broadside if they've been raised on 'Murikan NRA-Jesus ideas. If they are bottom-line economic arguers, Universal Healthcare is the only way we are going to tamp down on runaway wasteful administrative costs and massive profits going to insurance company shareholders for which the rest of us end up footing the bill. This is not hypothetical. Literally the entire rest of the developed world has figured this out. It is only narrow greedy capitalist interests that have kept a strangle hold on the United States. Yay team?
Education is a tougher question, because the effects/benefits don't become obvious for quite a few years, but literally the dumber our workforce, the less competitive American business and industry is in the world; less flexible, more dependent on competing with other low-paid worker countries rather than benefiting from quality creative and skillful employees. Neglecting widespread quality education literally means settling for mediocrity as a nation. Why would we do that? Again, it goes back to narrow greedy interests and the fears those interest groups manage to sell to the broader electorate to keep people voting against what is in their own economic interest.
You might take a look at America's uniquely flourishing Prison Industry. We are spending a massive amount of tax money on incarceration. There are surely multiple reasons, including racism, but there is a strong argument to be made for the idea that the shrinking middle class and ever-growing ranks of the poor in a fabulously wealthy consumerist society is the core reason behind this embarrassing state of affairs. We are not a civil society if we have such grotesque disparity in our society. Education is perhaps the biggest key to escaping poverty. Paying for education and paying for healthcare, not to mention socialized daycare subsidies and a clean environment, are core infrastructure components to a society that wants to encourage entrepreneurial creativity and energy.
Just think about capitalist society in which basic sustenance for life exists as a baseline social safety net. People can afford to take risks in business if they know the bare basics will still be there for them. Why saddle American businesses with the financial pressure of health care plans for employees. Other countries don't do this.
Socialism doesn't mean spreading all the wealth evenly regardless of who has done what work. It simply means certain key social infrastructure is important enough to be considered of interest to all and therefore worthy of being covered by the whole society.

Virtually every industrialized nation has a form of universal healthcare, and their per capita costs are a lot lower than ours yet provide care to everyone.

I’d assumed ‘universal healthcare’ would free up more intrapreneurs … allowing them to chance starting a business without lacking health care in the meantime. And, allowing successful business to avoid dealing with providing it, or not. Also, I’d expect there’d (once again) be public service campaigns encouraging US citizens to shape up, if only to keep the overall costs down.

I’d thought, and still think Obama’s plan for the first 2 years of community college to be ‘free,’ or at least an extension of our current K-12 ‘free education’ was an excellent plan whose time has definitely come. If you desire an additional 2 years, or more, it’s on ‘you.’ Otherwise, society invests in its future citizens.